The Best Bad Boy Around

I have to admit, I’ve been meaning to write for some time, but I’ve been lacking inspiration. I really should have just looked in front of my face. With the new revival coming up and a coworker beginning her first viewing of the series, both of which spurred my own rewatch, I have had Gilmore Girls on the brain lately.

Now I know Gilmore Girls may not be terribly familiar to this audience, but here’s what you need to know for now. Jess is the Best.


Jess, played by Milo Ventimiglia, is the quintessential intellectual bad boy; he’s got a troubled past, doesn’t like small talk, and is more likely to sass than not, but he also gets his life together in a big way. He’s the best bad boy around.

While Jess is immediately recognizable as the resident rebel with his James Dean glare, black leather jacket, and carefully coifed hair…the rest of his wardrobe is pretty…normal.


There’s a lot of dark colors, ribbed sweaters, and so, so many layers. But even a yellow/gold coat can work for a bad boy with the right amount of snark and disregard. But he plays up his assets. The neutral colors don’t pull focus away from his face. Pushed up sleeves, tight-ish sweaters, and bulky watches draw attention to his arms.

His hair changes length through out the series, but always remains artfully disheveled. When it’s short, he uses product. When it’s long, he keeps it out of his face.

And while his jeans might be a little loose by modern trends, and some of his shirts scream mid-2000s, a lot of it is quality basics.


Mimic Jess with hoodies under leather jackets, or maybe even different types of sweaters. Trade the classic mid-2000s look of a long-sleeved shirt under a short-sleeved shirt for a black or white v-neck.

Jess Mariano’s wardrobe matured as he did, and I can’t wait to see where his life and wardrobe have gone in the past eight years.

#JessistheBest #TeamJess


To nail the literary part of this intellectual bad boy’s look, keep an eye out for a literary gents post that I am desperately trying to complete.

As always, please send requests for things you’d like to see!



Bomber Jackets

Bomber jackets, or flight jackets, got their start keeping fighter pilots warm during World War I, and with a heritage like that, they can’t be anything but cool.

They have, however, come a long way since then. They are now lighter weight, not the heavily insulated jackets of old, and more of a fashion piece than utilitarian. You can find more traditional looking ones, worn leather, with a looser shape, but generally the term “bomber jacket” has come to refer to most collarless jackets, with a loose shape (varsity jackets are similar).

bomber jacket

In recent years bombers have become the staple style of jacket for brighter colors and wilder patterns, but it works in almost any configuration. Solid colors, sleeves that are a different color, varsity stripes on the collar, it pretty much all works.

They also pair with almost all looks, from semi-formal to casual, so they can be thrown over most things.

bomber jackets

All buttoned up Or…

So I kind of touched on this in my last post, but I’ve noticed two competing trends in menswear: The buttoned all the way up and the letting some chest show. Now obviously you are all buttoned up when you are wearing a tie, so this is for more casual, non-tie days. I honestly don’t have a preference between the two, they are just different looks, but I’ll try and offer some tips on how to do both properly.

I first saw the top-button-done look during my time in England, so I still associate them, and while it is steadily working its way across the Atlantic it is still a look that reads a British aesthetic.

This look take commitment because if done with the wrong shirt it  could look like you just forgot your tie. For that reason I suggest more casual shirts, be they chambray or short-sleeved. Also I would say it is easier to pull-off when the shirt is tucked in, but that doesn’t mean un-tucked is totally out of the question.

All buttoned up is definitely complemented best by skinny or slim cut jeans to keep the correct proportions. In general men want to have a V shape; the top-button-done narrows the top, so you want to balance it with a narrow bottom.

all buttoned up

Now for the opposite side of the spectrum. Another thing that’s making a comeback? Chest hair. Believe me, I never thought I’d say those words. However, we are not talking Pierce Brosnan in Die Another Day, but something more manly and less caveman-y.

Like I mentioned in the Tom Mison Spotlight, you just want a glimpse of the chest, not a full-frontal accost. We are talking the top three or so buttons undone (top two is pretty standard and top four could be too much).

This is a sexy and confident look that draws attention up to the face. It also elongates your torso a bit and makes your shoulders seem wider. All pluses, but it can veer into disco or pirate, so be tasteful. Wear with slim fit pants, but not skin-tight.

Three undoneI’m also going to include wide-necked shirts in this latter category because what we are really after here is collar-bones. For some reason showing off the clavicle is super sexy on a man or woman. The same open neck effect of the slightly un-buttoned can be achieved with a V-neck, boat neck, or other wide necked t-shirts and sweaters. Henleys are good for this.

the wide neck route(Hello Tom Mison’s eyebrows)

A great neck for Joel McHale